Updated May 26, 2023 - Things to Do

Old Town Art Fair voted Chicago's best street festival

A crowd of people walk by white tents.
Photo courtesy of the Old Town Art Fair

The Old Town Art Fair was crowned the best Chicago street fest in Axios' unofficial tournament bracket challenge.

Why it matters: Street festival season is among Chicago's best summer traditions, when streets are closed to erect tents, stages and kids' bouncy houses.

State of play: Axios Chicago narrowed down the city's hundreds of street festivals to a top 16, and asked readers to pick which event reigns supreme.

  • Here's how it played out:
Bracket: Axios Visuals
Bracket: Axios Visuals

Methodology: We didn't include Taste of Chicago or the bigger festivals that surround the parades.

  • The other rule: It has to take place on the street. That eliminates some heavy hitters like the Silver Room Block Party (now at Oakwood Beach) and Taste of Polonia (parking lot of the Copernicus Center).
  • Also, no suburbs.

Catch up on how each round played out:

The championship

After a week of hard-fought battles, the final two street festivals standing in our quest to crown the best were:

  • Old Town Art Fair vs. Printers Row Lit Fest.

Old Town Art Fair: This early June festival breezed past the Sheffield Garden Walk to get to the finals. It bills itself as one of the nation's oldest art fairs, embedded along beautiful Old Town side streets.

  • The fair presents a mixture of art, community and architecture, along with beers in plastic cups.

Printers Row Lit Fest: This early September event used to be called Printers Row Book Fair, but it's always offered a place for authors and fans of the written word to convene along the picturesque streets in Printers Row and the South Loop.

  • Highlights include talks, panels, demonstrations and signings with local and touring writers — including Monica this year.

Final Four

Readers chose cultural festivals over the "cover band and a beer" classic events in the Final Four.

What happened: The Old Town Art Fair needed little time to oust Wicker Park Fest, while Sheffield Garden Walk pulled out the win over the Pilsen stalwart Fiesta del Sol.

  • The other side of the bracket had the Printers Row Lit Fest easily handling the 57th Street Art Fair, while the Andersonville Midsommarfest moved on, defeating Do Division.

Elite Eight

Here's how readers narrowed down the list to eight street festivals:

Biggest win: Printers Row Lit Fest got 81% of the vote in the matchup against Edison Park Fest.

Closest wins: The 57th Street Art Fair slipped by Taste of Randolph by only two votes, while Fiesta del Sol barely hung on to best the Taylor Street Festival.

Most surprising win: Sheffield Garden Walk easily beat West Fest (56%-44%).

Editor's note: This story was updated to add details on the latest tournament rounds.


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